Flash forward to the present day and the story could not be more different. De Botton is the good-looking darling of the upper-class literary establishment. He has written three books since Cambridge: Essays in Love; The Romantic Movement and now, due out this week, Kiss and Tell. The first two - both about love; both part narrative, part philosophy, part psychology - have met with noisy success. Both are translated into 14 languages - "the factor which enables me to keep going" - and the critics, at least those that matter in commercial, fashionable highbrow literary spheres (Vogue, Tatler and the broadsheets) have gone berserk. The tabloids, in predictable aphoristic form, have labelled him "Dr Love".
Yet De Botton's success has not been unequivocal. Though rightly acclaimed as something of a literary entrepreneur for daring, in his early twenties, to write authoritatively about the psychology of love (Cambridge provided him with a girlfriend), the literary and philosophical allusions that litter his work have laid him open to accusations of pretension. Some of his peer group has even labelled him, unkindly, Alain "I have read some Proust" de Botton.
The trouble is not his literary method, but his delivery of it. In his second book, The Romantic Movement, De Botton explains a mundane lovers' tiff by pondering on Rousseau's theory of naturalism. The comparison provides an astute original insight into the workings of the human mind, but De Botton's Rousseau ramble is so long that it loses all relevance to the narrative and makes him - the authority on Rousseau - look like a show- off. "Few readers," said a review in the Times "enjoy having the superiority of the author thrust down their throats."
Kiss and Tell, though, is different. It is not about the psychology of love so much as the psychology of getting to know another person, and how intrinsically impossible it is to do that properly. Not a difficult idea but, typically, De Botton makes it clever, by playing with the medium of biography.
The narrator, spurned by a girlfriend for his inability to empathise, decides to amend matters by writing a biography of the next girl he meets. This is Isabel, a production assistant in her twenties. He tries all the conventional forms; he starts with her birth, talks about her family, progresses through school and so on. He even tries to write a description of her in one of those lonely-heart newspaper-advertisement boxes, but nothing truly manages to capture the real Isabel, other than when she is talking, breathing, living her idiosyncratic self.
"We live in an age that is so intent on calculating things, of putting them into boxes," says De Botton when we meet in the chairman's office at Macmillan, adding, somewhat disarmingly, "You, for instance, will have to do a word count when writing up this interview.
"Things are getting more calculated than the modes we build for them. I enjoyed building a model that breaks down. Biography in particular is the culturally dominant form that wants to wrap a life, but in reality life just seeps out the sides."
Kiss and Tell's main attraction lies in the characterisation of Isabel. She is so very lovable, so very dotty and utterly unpredictable. On meeting the narrator for the second time ever, she does not suggest dinner or lunch but that they go for a swim together, in a public pool in Hammersmith (she is trying to keep in shape). While being splashed by a group of children on the second lap she asks the narrator, "Do you know something odd? Both Camus and Beckett really loved sport. Camus was a goalkeeper for the Algerian football team and Beckett was in Wisden for having done something great in cricket."
De Botton breaks out into a huge grin when this episode is mentioned: "Yes, it is meant to be funny," he smiles. "Of course she hasn't read a word of Camus - she just heard it somewhere ... but, you know, people do talk about very odd things very easily. You don't have to go on safari with a notebook to work that out; you just hear it all around you."
The suave, sophisticated empiricist before me (his manners - door-holding to knife-holding - are impeccable) has clearly long replaced the Cambridge swot and, these days, he appears even to have a sense of humour about his subject matter. At one point in Kiss and Tell, there is, astonishingly, a joke about the tedium of Proust (De Botton's favourite author - he gets a mention in every book, his name crops up 11 times in this index and he is the subject of De Botton's next book). "Unfortunately," says the narrator when it emerges his companions could not plough through the whole text,"I too had not read more than 20 pages ...."
"Bits of Proust are boring," says De Botton "and so why not say so? I quote him and other writers in the spirit of fun rather than anything else. It's a way of making a point in quite a charming, pleasant way; it's a way of focusing an anecdote, to keep the reader amused, because it amused me."
Kiss and Tell is a very funny book, precisely because this time the sparing philosophical references are witty, insightful and original. "I did try this time," De Botton admits "to achieve the right level of lightness; to touch on an intellectual idea and to move on, not belabour the point as one might in an essay. Just make it a rapid reading."
But such zealousness to appease his critics is one of the signs that De Botton has found the accusations of pretension extremely difficult to take. He begins a defence of his work on that count, before I even ask for it. And he stumbles, tripping over his words, not out of hesitation or insecurity, but simply because he is so keen to get it all out: "I do not think my books are pretentious. There's always a suspicion with anything that is philosophical/ psychological that it might be considered so. But it is kind of insulting to readers, and to people generally, if every time we mention something a bit serious we are deemed pretentious ... It is as if people are saying you can't talk about this because you don't know enough about it. I think that is so damaging.
"What I'd really like to do is to lead people into quite serious ideas but so that they are not made frightening and so that they are relevant ... because they are genuinely relevant to me." He has been angrily bashing his pen on his palm throughout this outburst and, as we go on to talk about his youth and background, just occasionally his carefully constructed mask slips. One begins to understand the intellectual isolation that has made him so defensive about being clever.
An unhappy, inappropriate schooling at Harrow - "it was like a borstal, it showed me the worst side of the English aristocracy"- resulted in a wariness of everybody, including family and friends, because of fear of appearing too different, too intellectually daring or superior. "When I first decided to write a book just after Cambridge," he says revealingly, "I gave myself six months and didn't tell anyone because people treat you like an alien once you do. It's as if you've got Aids."
Now his peer group seeks him out. He has become the romantic idol of the twentysomething Oxbridge circuit. But still there is something in De Botton's demeanour which does not sit easily with that. His dark eyes have a constantly troubled look and he always answers the phone breathless with anxiety. But then, he agrees, that pain is an essential prerequisite for writing. "Far too many people do not suffer when they should," he says." I think a writer needs to find things slightly difficult, because, well, so many things in life are."
n 'Kiss and Tell' (Macmillan, pounds 9.99) is published tomorrowReuse content